It’s 2 AM on a Saturday night in the spring of 2001, and 28-year-old Cecily Gardner sits alone in a dive bar in New York’s East Village, questioning her life. Feeling lonesome and homesick for the Midwest, she wonders if she’ll ever make it as a reporter in the big city - and whether she made a terrible mistake in breaking up with her longtime boyfriend, Matthew.

Nina Browning is living the good life after marrying into Nashville's elite. More recently, her husband made a fortune selling his tech business, and their adored son has been accepted to Princeton. Yet sometimes the middle-class small-town girl in Nina wonders if she's strayed from the person she once was. Tom Volpe is a single dad working multiple jobs while struggling to raise his headstrong daughter, Lyla. His road has been lonely, long, and hard, but he finally starts to relax after Lyla earns a scholarship to Windsor Academy, Nashville's most prestigious private school.

Four freshmen arrive at college from completely different worlds: Lainey, a California party girl with a flair for drama; Tyson, a brilliant scholar and aspiring lawyer from Washington, D.C.; Summer, an ambitious, recruited athlete from the Midwest; and Hannah, a mild-mannered southerner who is content to quietly round out the circle of big personalities. Soon after arriving on campus, they strike up a conversation in their shared dorm, and the seeds of friendship are planted.

Tessa Russo is the mother of two young children and the wife of a renowned pediatric surgeon. Despite her own mother's warnings, Tessa has recently given up her career to focus on her family and the pursuit of domestic happiness. From the outside, she seems destined to live a charmed life. Valerie Anderson is an attorney and single mother to six-year-old Charlie - a boy who has never known his father.

Growing up, Josie and Meredith Garland shared a loving, if sometimes contentious, relationship. Josie was impulsive, spirited, and outgoing, Meredith hardworking, thoughtful, and reserved. When tragedy strikes, their delicate bond splinters.

Ellen and Andy's first year of marriage doesn't just seem perfect, it is perfect. There is no question how deep their devotion is, and how naturally they bring out the best in each other. But one fateful afternoon, Ellen runs into Leo for the first time in eight years. Leo, the one who brought out the worst in her. Leo, the one who left her heartbroken with no explanation. Leo, the one she could never quite forget. When his reappearance ignites long-dormant emotions, Ellen begins to question whether the life she's living is the one she's meant to live.

When her twenty-two-year-old stepdaughter announces her engagement to her pandemic boyfriend, Sarah Danhauser is shocked. But headstrong Ruby has already set a date (just three months away!) and spoken to her beloved safta, Sarah’s mother Veronica, about having the wedding at the family’s beach house in Cape Cod. Sarah might be worried, but Veronica is thrilled to be bringing the family together one last time before putting the big house on the market. But the road to a wedding day usually comes with a few bumps

First comes love. Then comes marriage. Then comes...a baby carriage? Isn’t that what all women want? Not so for Claudia Parr. And just as she gives up on finding a man who feels the same way, she meets warm, wonderful Ben. Things seem too good to be true when they fall in love and agree to buck tradition with a satisfying, child-free marriage. Then the unexpected occurs: one of them has a change of heart.

Sasha has had it. She cannot bring herself to respond to another inane, “urgent” email or participate in the corporate employee joyfulness program. She hasn’t seen her friends in months. Sex? Seems like a lot of effort. Even cooking dinner takes far too much planning. Sasha has hit a wall. Armed with good intentions to drink kale smoothies, try yoga, and find peace, she heads to the seaside resort she loved as a child. But it’s the off season, the hotel is in a dilapidated shambles, and she has to share the beach with the only other occupant: a grumpy guy named Finn.

After being together for 10 years, Sylvie and Dan have all the trimmings of a happy life and marriage; they have a comfortable home, fulfilling jobs, and beautiful twin girls and communicate so seamlessly, they finish each other's sentences. However, a trip to the doctor projects they will live another 68 years together, and panic sets in. They never expected "until death do us part" to mean seven decades. In the name of marriage survival, they quickly concoct a plan to keep their relationship fresh and exciting.